1. Field of the Invention
The present invention relates to novel ethylenically unsaturated amine salts of sulfonic, phosphoric and carboxylic acids. More specifically, the invention relates to ethylenically unsaturated amine salts of alkylbenzene sulfonic acids, alkyl olefin sulfonic acids, alkyl alcohol sulfuric acid esters and alkoxylated alkyl alcohol sulfuric acid esters, and mixtures thereof. Additionally, the invention relates to ethylenically unsaturated amine salts of alkyl carboxylic acids and alkyl phosphoric acids. The salts are polymerizable, surface active agents which are useful in a variety of applications, especially in detergent formulations and in emulsion polymerization processes.
2. Description of the Related Art
Detergents, shampoos, cleansers, soaps, and the like, are used to perform a wide variety of household and industrial cleaning operations and are formulated to give compositions which produce optimum performance under the contemplated end use conditions. Typically, these compositions contain a variety of surface active agents known to the art, in the form of anionic, nonionic, amphoteric, and/or cationic surfactants. The anionic surfactants used in the compositions are typically in the form of alkali metal (lithium, sodium, potassium), alkaline earth (calcium, magnesium), ammonium and/or alkanolamine salts of the corresponding anionic acid. In formulating such compositions, it is desirable to have a variety of surface active agents available for producing and optimizing the compositions.
Surface active agents also find use in applications beyond typical detergent or shampoo formulations. For example, in a conventional emulsion polymerization of ethylenically unsaturated monomers, one or more surfactants are used to emulsify the monomers and the resulting polymer products, i.e., latexes. The monomers used in emulsion polymerization reactions are generally water-insoluble, but may also be water-soluble. During the polymerization, small portions of monomer are suspended in a continuous aqueous phase. Typically, a water soluble surfactant is present within the aqueous phase to aid in the suspension of the monomer, with subsequent polymerization via a free-radical polymerization. The water soluble surface active agents, i.e., surfactants, utilized in emulsion polymerization reactions are typically anionic, nonionic, cationic, or zwitterionic surfactants or mixtures thereof.
In a traditional emulsion polymerization reaction, discrete, solid polymeric particles are formed during the course of the reaction to form a polymer product latex. Typically, the surfactant employed in such a traditional emulsion polymerization reaction does not react with, i.e., become chemically bonded via carbon-carbon bond formation, the discrete polymeric particles. Rather, the surfactant remains unreacted in the polymer product latex after the emulsion polymerization reaction is complete. The unreacted surfactant can interfere with the performance of such polymerization products in coating, adhesive, sealant and elastomer (CASE) applications, non-woven fiber applications and carpet backings. The unreacted surfactant may cause pealing of a latex paint coating, and decreased moisture resistance and scrubability resistance in various CASE applications. Additionally, residual surfactant can cause an undesirable “blooming” that leads to surface irregularities in a resulting CASE that is applied to a substrate.
Several proposals have been made in the prior art to employ a polymerizable surfactant as the surface active agent during an emulsion polymerization reaction. U.S. Pat. No. 5,478,883 (incorporated herein by reference) describes the use of ethylenically unsaturated polymerizable water-soluble nonionic surfactants formed by the reaction of a diallylamine compound with ethylene oxide, propylene oxide or butylene oxide, in emulsion polymerization reactions. Similarly, U.S. Pat. No. 5,162,475 (incorporated herein by reference) provides alpha-beta ethylenically unsaturated poly(alkylenoxy) polymerizable surface active compounds for use in emulsion polymerization. For additional examples of polymerizable surfactants for use in emulsion polymerization processes, see U.S. Pat. Nos. 4,377,185 and 4,049,608.